WASHINGTON — President Trump has been briefed repeatedly. His advisers have alerted him to the web of potential risks, complex issues and diplomatic snags.
But even his top aides do not know precisely what Mr. Trump will decide to say or do when he meets President Vladimir V. Putin of Russia face-to-face this week on the sidelines of the Group of 20 economic summit gathering in Hamburg, Germany. And that is what most worries his advisers and officials across his administration as he embarks Wednesday on his second foreign trip, first to Warsaw and then to Hamburg.
The highly anticipated conversation with Mr. Putin on Friday is in many ways a necessity, given the critical disputes separating the United States and Russia. But it is also a diplomatic and political risk for Mr. Trump, who faces a web of investigations into his campaign’s possible links to Russia, as well as questions about his willingness to take on Moscow for its military misdeeds and election meddling on his behalf. The air of uncertainty about the meeting is only heightened by the president’s tendency for unpredictable utterances and awkward optics.
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If Mr. Trump’s first foreign trip in May was a chance for him to escape turmoil at home — staff infighting, a stalled agenda and the Russia-related investigations — his second thrusts him into the maelstrom. And at the center of it, Mr. Putin awaits.
“There’s a fair amount of nervousness in the White House and at the State Department about this meeting and how they manage it because they see a lot of potential risks,” said Steven Pifer, a former ambassador to Ukraine who has worked for the National Security Council and the State Department. “There is this gray cloud for the president of the investigations about collusion, so any kind of a deal is going to get the micro-scrutiny of, ‘Is this a giveaway to the Russians?’”
Mr. Trump himself is not troubled by the meeting. He has told aides he is more annoyed by the prospect of being scolded by the German chancellor, Angela Merkel, and other leaders for pulling out of the Paris climate accords and for his hard line on immigration.
Mr. Trump’s team said he might bring up Russia’s documented meddling in the 2016 election, but he is unlikely to dwell on it: Doing so would emphasize doubts about the legitimacy of his election. Aides expect him to focus on Syria, including creating safe zones, fighting the Islamic State and confronting Mr. Putin’s unwillingness to stop the government of President Bashar al-Assad from using chemical weapons against civilians.
A day before Mr. Trump was to leave Washington, the White House announced that the meeting with Mr. Putin would be a formal bilateral discussion, rather than a quick pull-aside at the economic summit meeting that some had expected.
The format benefits both. Mr. Putin, a canny one-on-one operator who once brought a Labrador to a meeting with Ms. Merkel because he knew she was afraid of dogs, will be able to take the measure of Mr. Trump.
Mr. Trump’s aides are seeking structure and predictability. They hope that a formal meeting, with aides present and an agenda, will leave less room for improvisation and relegate Russia’s meddling in the campaign to a secondary topic, behind more pressing policy concerns that the president is eager to address.
“Nobody has found the slightest evidence of collusion, any evidence the vote was tampered with, so now they have turned their obsession to Russian ‘interference,’” said Kellyanne Conway, the president’s senior counselor and former campaign manager. “I don’t think that’s what the American people are interested in.”
Mr. Trump’s meeting with Mr. Putin is one of several charged encounters he will face in Hamburg. After North Korea’s announcement on Tuesday that it had successfully tested its first intercontinental ballistic missile, his planned huddle with President Xi Jinping of China took on greater significance, as Mr. Trump bristles at Beijing’s refusal to do more to confront the nuclear threat from North Korea and weighs his limited options for acting alone. He is also planning private discussions with Prime Minister Shinzo Abe of Japan and President Moon Jae-in of South Korea that are certain to center on the North’s continued provocations.
But the political stakes could not be higher for Mr. Trump in his meeting with Mr. Putin, as lawmakers in both parties press him to stand tough. They signaled their wariness last month with a 98-2 vote in the Senate to codify sanctions against Russia and require that Congress review any move by the president to lift them, a step the White House is resisting.
“Let’s be clear: The Russians interfered in our election and helped elect Donald Trump president,” said Senator Jack Reed, Democrat of Rhode Island and the ranking member of the House Armed Services Committee. “There is a serious, ongoing criminal investigation into this matter. And President Trump must refrain from any unilateral concessions to Russia.”
Cognizant of the perils, the White House has planned Mr. Trump’s itinerary to counter the perception that he is too friendly with Moscow. In Warsaw on Thursday, he will deliver a major speech and meet with Central and Eastern European allies, activities calculated to demonstrate his commitment to NATO in the face of Russian aggression. But there, too, Mr. Trump will be under pressure to do what he refused to in Brussels during his first trip: explicitly endorse, on European soil, the Article 5 collective defense principle that undergirds NATO.
His advisers say that he is eager to meet with President Andrzej Duda of Poland, a center-right politician who shares Mr. Trump’s skepticism about migration from Syria, and that he sees a chance to make lucrative energy deals with Mr. Duda’s government — perhaps at the expense of Russia.
But the substance and body language of his encounter with Mr. Putin will draw the most scrutiny.
“I expect an Olympian level of macho posturing between these two leaders, who both understand the power of symbolism,” said Derek Chollet, a former assistant secretary of defense. “Putin will be very prepared for this meeting. He’s someone who is a master at manipulation.”
Mr. Putin has signaled that he will press Mr. Trump to lift sanctions imposed on Russia for its annexation of Crimea, its interference in Ukraine and its election meddling, and to hand over Russian diplomatic compounds on Long Island and in Maryland that the United States seized last year.
The potential pitfalls are more than theoretical. White House officials recall with dread the images that emerged from Mr. Trump’s May meeting with Foreign Minister Sergey V. Lavrov and Ambassador Sergey I. Kislyak of Russia in the Oval Office, which showed the president grinning, laughing and clasping hands with the Russian officials.
The biggest concern, people who have spoken recently with members of his team said, is that Mr. Trump, in trying to forge a rapport, appears to be unwittingly siding with Mr. Putin. Like Mr. Trump, Mr. Putin has expressed disdain for the news media, and he asserted in a recent interview that secretive elements within the United States government were working against the president’s agenda. Two people close to Mr. Trump said they expected the men to bond over their disdain for “fake news.”
“You don’t want to come out of there saying, ‘We’re friends, and the enemy is the deep state and the media,’” said Michael A. McFaul, a former ambassador to Russia. “If it were somebody else other than Trump, you could imagine a tough conversation about Ukraine and election meddling, but that’s probably too optimistic. Politics does constrain, I think, the parameters of the possible for any kind of major breakthrough.”